Carbon Dioxide → 1,5-Bis(p-chlorobenzenesulfonyl) carbohydrazide

HRID 839479Notes

Reaction equation

HRID 839479 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][NH:13][C:14]([NH:16][NH2:17])=[O:15].C(=O)(O)[O-].[Na+].C(=O)=O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][NH:13][C:14]([NH:16][NH:17][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 73984-Chlorobenzenesulfonyl chlorideHCID 73948CarbohydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 706065491,5-Bis(p-chlorobenzenesulfonyl) carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

211 g (1.0 mole) p-chlorobenzenesulfonyl chloride was added to a suspension of 45 g (0.5 mole) carbohydrazide and 100 g sodium bicarbonate in 1000 ml ethanol in a 3 liter reaction flask. The mixture was stirred and heated gradually to gentle reflux (80° C) as carbon dioxide was evolved. Heating was continued until CO2 no longer evolved (3 hours). The mix was cooled to 20° C and filtered. The mixture of product and sodium chloride was dried at 60° C. Yield = 227 g. The solid mixture was suspended in 2000 ml water, stirred to dissolve the sodium chloride, and then the insoluble product was filtered, washed and dried. Yield = 129 g, m.p. 239°-240° C (dec.)

Workup

  1. temperatureheated gradually
  2. temperatureHeating
  3. custom(3 hours)
  4. filtrationfiltered
  5. additionThe mixture of product and sodium chloride
  6. customwas dried at 60° C
  7. stirringstirred
  8. dissolutionto dissolve the sodium chloride
  9. filtrationthe insoluble product was filtered
  10. washwashed
  11. customdried

Sources & evidence

ORD record
ord-4bc19d05267b4ac8a1ec601404ffc0ad
Source dataset
uspto-grants-1978_06
Patent number
US04096100

Reaction notes

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